Is it better to purchase the windows, and DIY or hire a handyman? Or are the window "installers" worth the money?Where should I look (type) for a match to aluminum ?? Want it to look somewhat the same and these are to be retrofit.

I'd agree with masterext. If you search wisely, you can usually find a good deal from a window company/exterior remodeler... Not all of us are high-pressure, high-price. ... If that is not an option, you are probably better of DIY if you are mechanically inclined than paying some handyman who knows about as much as you.

Where are you located?If you are aiming for better thermal performance then you should look at fiberglassIf you do not care about thermal performance you should just get aluminum.Are you concerned with glass to frame ratio?

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